degradation reference materials 2021

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Degradation reference materials 2021.N-oxides

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Welcome to Mikromol’s degradation reference standards with a focus on N-oxides.

Active pharmaceutical ingredients (APIs) containing nitrogen as an amine are prone to degrade into N-oxides readily and quickly under oxidative stress.

Mikromol’s impurity reference standards are designed to be used at all relevant stages of the testing chain. The use of our N-oxide impurity standards facilitates assessment of the oxidative stress a particular product has been subjected to, the purity of the originating API, and helps determine the shelf life of the product.

Each impurity is accompanied by a detailed certificate of analysis, providing all the information you need to best use the reference material. Our products can be used with confidence during analytical research and development and validation studies, as well as for stability monitoring and routine quality control purposes.

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To find out more contact your local Mikromol office.

Mikromol provides a range of N-oxideimpurityreferencestandards formore than

major APIs.180

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Products – N-oxides

A. Amiodarone Hydrochloride — Azaperone

B. Bamifylline Hydrochloride — Butorphanol Tartrate

C. Carbinoxamine Maleate — Cyproheptadine Hydrochloride D. Deanol Acetamidobenzoate — DroperidolE. Ebastine — Escitalopram Oxalate F. Fentanyl — Furaltadone G. Gefitinib – Granisetron Hydrochloride H. Halofantrine Hydrochloride — Hyoscyamine SulfateI. Imipramine Hydrochloride K. Ketoconazole — Ketotifen Hydrogen Fumarate L. Lansoprazole — Loxapine SuccinateM. Mebhydrolin Napadisilate — Mycophenolate Mofeti N. Nalbuphine Hydrochloride — Nikethamide O. Ofloxacin — Oxycodone HydrochlorideP. Pantoprazole Sodium

Sesquihydratel — Proxymetacaine Hydrochloride

Q. Quetiapine Fumarate — Quinine HydrochlorideR. Rabeprazole Sodium — Rotigotine HydrochlorideS. Sildenafil Citrate — Sumatriptan SuccinateT. Tamoxifen Citrate — TropicamideV. Vardenafil Hydrochloride Trihydrate — VinpocetineX. Xanthinol NicotinateZ. Zolmitriptan — Zopiclone

Formation of Omeprazole Sulphone by oxidative degrada-tion of Omeprazole (Imp. D (EP): 5-Methoxy-2-[[(4-meth-oxy-3,5-dimethylpyridin- 2-yl)methyl]sulphonyl]-1H-ben-zimidazole (Omeprazole Sulphone), MM0095.05)

Degradation products - N-oxidesCAS No. CS UnitProductProduct Code

Amiodarone Hydrochloride

MM0697.10 Amiodarone N-Oxide Hydrochloride n/a 100mg HClI

ON

+ O

I

O

O

Amitriptyline Hydrochloride

MM0062.12 Amitriptyline N-Oxide Hydrochloride 4290-60-2 10mg H C lN+

O

Amodiaquine Dihydrochloride Dihydrate

MM0617.08 Amodiaquine N-Oxide 102391-07-1 100mgN

NH

N+

O

OH

Cl

Aripiprazole

MM0961.03-0025Imp. F (EP): 7-[4-[4-(2,3-Dichlorophenyl)-1-oxidopiperazin-1-yl]butoxy]-3,4-dihydroquinolin-2(1H)-one (Aripiprazole N-Oxide)

573691-09-5 25mgO

N+

N

Cl

Cl

O NH

O

Atropine

MM0289.19 Atropine N-Oxide Hydrochloride 4574-60-1 100mgO H

O

O

H

H

H

N+

O HCl

AND Enantiomer

Azaperone

MM1164.01 Azaperone N-Oxide 66065-28-9 100mgN

N

N +

F

O

O

Azithromycin

MM1075.10-0025 Imp. L (EP): Azithromycin 3 -N-Oxide 90503-06-3 25mg

N

OH

O H

O

OO

O

OH O

OO

N+

O

O H

OH

Bamifylline Hydrochloride

MM1823.01 Bamifylline N-Oxide n/a 100mg N

O

N

N+OH

O

NNO

Benactyzine Hydrochloride

MM1826.02 Benactyzine N-Oxide 42771-70-0 100mgOH O

ON+ O

A-1 ISO 17034 | ISO 17025 | Edition 1/2021 | Visit us at lgcstandards.com/mikromol or email to [email protected]

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Benperidol

MM0113.09 Mixture of Imp. D and E (EP): Benperidol N-Oxide(cis and trans) 118435-01-1 25mg

F

O

N+

O

N

NHO

Benztropine Mesilate

MM1227.02 Benztropine N-Oxide Hydrochloride n/a 100mg HCl

O

H

H

H

N +O

Benzydamine Hydrochloride

MM0142.08 Benzydamine N-Oxide Hydrochloride 39860-94-1 100mg HClN

N

O N+

O

Biperiden Hydrochloride

MM0288.07 Biperiden N-Oxide n/a 100mgH

H H OH

N +O

AND Enantiomer

MM0288.08 Biperiden Epoxide N-Oxide n/a 100mgH

H

O

H OH

N+O

AND Enantiomer

Bromhexine Hydrochloride

MM0065.09 Bromhexine N-Oxide n/a 100mgBr

N+

ON H 2

Br

Brompheniramine Maleate

MM0060.18 Brompheniramine N-Oxide Dihydrochloride n/a 100mg 2HCl

N

Br

N+

O

MM0060.19-0100 Brompheniramine N-Oxide Maleate n/a 100mgO H

O

O H

O

ON

+

Br

N

Buflomedil Hydrochloride

MM0066.12 Buflomedil N-Oxide Hydrochloride n/a 100mg HCl

O

N+OO

OO

Bupivacaine Hydrochloride

MM0613.07 Bupivacaine N-Oxide 1346597-81-6 100mg NH

N+

OO















Buprenorphine

MM0120.15 Buprenorphine N-Oxide 112242-17-8 100mgN+O

OOH O

OH

H

Buprenorphine Hydrochloride

MM0120.15 Buprenorphine N-Oxide 112242-17-8 100mgN+O

OOH O

OH

H

Buspirone Hydrochloride

MM0464.31-0025 Buspirone N-Oxide Oxalate 1797880-63-7 25mg OHO H

O

O

O

NN

+O

N N

N

O

Butacaine Sulfate

MM1638.01 Butacaine N-Oxide n/a 100mg N+

O

O

NH 2

O

MM1638.02 Butacaine N-Oxide Hydrochloride n/a 100mg HClO

N+

O

NH2

O

Butalamine Hydrochloride

MM1845.02 Butalamine N-Oxide n/a 100mg N

ON

NH

N+

O

Butorphanol Tartrate

MM1192.01 Butorphanol N-Oxide 112269-63-3 100mgN

+O

OH

OH

Carbinoxamine Maleate

MM1135.01 Carbinoxamine N-Oxide 1256285-70-7 100mg N+O

Cl

NO

Cetirizine Dihydrochloride

MM0380.13 Cetirizine N-Oxide 1076199-80-8 100mgC l

N

N + OO H

OO

Chlorcyclizine Hydrochloride

MM1653.01 Chlorcyclizine N-Oxide 10457-56-4 100mgCl

N

N+

O















Chloropyramine Hydrochloride

MM1894.04-0025 Chloropyramine N-Oxide Hydrochloride n/a 25mg HCl

N+N

Cl

N

O

Chlorphenamine Maleate (Chlorpheniramine Maleate)

MM0090.15 Chlorphenamine N-Oxide Maleate n/a 100mgO

OH

O

OH

Cl

NN

+

O

Chlorphenoxamine Hydrochloride

MM1291.02 Chlorphenoxamine N-Oxide 110203-91-3 100mgCl

ON

+O

Chlorpromazine Hydrochloride

MM0420.02 Chlorpromazine Sulphoxide N-Oxide Maleate 150111-59-4 10mgO

O H

O

O HN

SO

N+

O

C l

MM0420.13 Chlorpromazine N-Oxide Hydrochloride n/a 100mg HCl

Cl

N N+

OS

MM0420.11 Chlorpromazine Sulfone N-Oxide Hydrochloride(Chlorpromazine N,S,S-Trioxide Hydrochloride) 109724-46-1 100mg H C l

C l

N N+

OSO

O

Cinchocaine Hydrochloride (Dibucaine Hydrochloride)

MM0604.05 Cinchocaine N-Oxide 87864-07-1 100mg N

NH

N +

O

O

O

Cinnarizine

MM1038.11 Cinnarizine N4-Oxide Dihydrochloride n/a 100mg 2HCl

N

N+O

Citalopram Hydrobromide

MM0242.10 Citalopram N-Oxide 63284-72-0 100mg

F

N+

OO

N

Clarithromycin

MM0057.17-0025 Clarithromycin N-Oxide 118074-07-0 25mgO

O

OHOH

O

OO

O

OH O

OO

N+O OH















Clindamycin Phosphate

MM1520.04 Clindamycin Phosphate Sulfoxide trans-N-Oxide n/a 100mg OHO

OH O P

OHOH

OS

O

NH

N+O

O

Cl

MM1520.05 Clindamycin Phosphate Sulfone trans-N-Oxide n/a 100mg OHO

OH O P

OHOH

OS

OO

NH

N+O

O

Cl

Clomifene Citrate (Clomiphene Citrate)

MM0650.01 Clomifene N-Oxide Hydrochloride 97986-33-9 100mgHCl

Cl

ON

+

O

Clomipramine Hydrochloride

MM0545.09 Clomipramine N-Oxide 14171-67-6 100mg N+

ON

Cl

Clozapine

MM0480.07 Clozapine N-Oxide 34233-69-7 100mg N

N+O

N

NH

Cl

Codeine Monohydrate

MM0004.01 Codeine N-Oxide 3688-65-1 CS 250mgN +

O

OO O H

H

Cyclizine Hydrochloride

MM1265.04 Cyclizine N-Oxide Dihydrochloride n/a 100mg 2HCl

N

N+

O

Cyclobenzaprine Hydrochloride

MM1248.03 Cyclobenzaprine N-Oxide Hydrochloride n/a 100mg HClO

N+

Cyclopentolate Hydrochloride

MM0580.05 Cyclopentolate N-Oxide Hydrochloride n/a 100mg HCl

O

ON

+O

OH














Cyproheptadine Hydrochloride

MM0609.05 Cyproheptadine -N-Oxide 54381-42-9 100mgN

+O

alpha-Isomer

MM0609.06 Cyproheptadine -N-Oxide 60251-34-5 100mgN

+O

beta-Isomer

Deanol Acetamidobenzoate

MM1681.01 Deanol N-Oxide 10489-99-3 100mgOH

N+

O

Dexchlorpheniramine Maleate

MM1114.03 Dexchlorpheniramine N-Oxide Dihydrochloride n/a 100mg 2HCl

Cl

N+

O

N

Dextromethorphan Hydrobromide

MM0033.11 Dextromethorphan N-Oxide Hydrochloride 1177419-85-0 100mg HCl

N+

O

H

O

Diethazine Hydrochloride

MM1593.08 Diethazine N-Oxide Hydrochloride n/a 100mg HClO

N+

N

S

MM1593.09 Diethazine Sulfoxide N-Oxide Hydrochloride(Diethazine N,S-Dioxide Hydrochloride) n/a 100mg HCl

O

N+

N

SO

MM1593.10 Diethazine Sulfone N-Oxide Hydrochloride(Diethazine N,S,S-Trioxide Hydrochloride) n/a 100mg HCl

O

N+

N

SOO

Difenidol Hydrochloride

MM3053.01 Difenidol N-Oxide 40220-79-9 100mg OHN

+O

Difloxacin Hydrochloride Trihydrate

MM3418.04 Difloxacin N-Oxide Sodium Salt n/a 100mgNa+

F

N

F

O

OO

N

N+O

Dihydrocodeine Hydrogen Tartrate

MM0812.08 Dihydrocodeine N-Oxide 109667-32-5 100mg H

O HOO

N+O
















Dimetindene Maleate

MM0595.13 Dimetindene N-Oxide Dihydrochloride n/a 100mg 2H C l

N

N +

O

Diphenhydramine Hydrochloride

MM0490.01 Diphenhydramine N-Oxide 3922-74-5 100mgO

N+ O

Diphenylpyraline Hydrochloride

MM0557.04 Diphenylpyraline N-Oxide 10020-59-4 100mgO

N+

O

Disopyramide

MM0108.09 Disopyramide N-Oxide Dihydrochloride n/a 100mg 2HCl

O

N+

N

N H 2

O

Domperidone

MM0107.09-0025 Domperidone N-Oxide 118435-03-3 25mgN

+

N

NHO

C lNNH

OO

Donepezil Hydrochloride

MM0677.14-0025 Donepezil N-Oxide 120013-84-5 25mgN+

O

O

O

O

Dosulepin Hydrochloride

MM0510.13 Dosulepin Sulfoxide N-Oxide Hydrochloride(Dosulepin N,S-Dioxide Hydrochloride) n/a 100mg

HCl

ON

+

SO

MM0510.14 Dosulepin Sulfone N-Oxide Hydrochloride(Dosulepin N,S,S-Trioxide Hydrochloride) n/a 100mg

HCl

ON

+

SO O

Doxapram Hydrochloride

MM0525.03 Doxapram N-Oxide n/a 100mgN O

N+

O

O














Doxepin Hydrochloride

MM0032.12 Doxepin N-Oxide Hydrochloride n/a 100mg HCl

O

N+

O

Doxylamine Hydrogen Succinate

MM0101.05 Doxylamine N-Oxide Dihydrochloride n/a 100mg 2HClN

ON+ O

Drofenine Hydrochloride

MM0768.01 Drofenine N-Oxide Hydrochloride n/a 100mg H C lO

N+

OO

Droperidol

MM0138.04Imp. D (EP) as Hydrochloride: (1RS)-1-[4-(4-Fluorophenyl)-4-oxobutyl]-4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1,2,3,6-tetrahydropyridine 1-Oxide Hydrochloride

n/a 100mg HClN+

N

NHO

F

O

O

Ebastine

MM0468.09 Mixture of Imp. Fand G (EP): Ebastine N-Oxide(cis and trans) 1256285-71-8 50mg

O

N+

O

O

Emedastine Difumarate

MM1277.09 Emedastine N-Oxide Difumarate n/a 100mg2

O

OHOH

ON

N

N

N+OO

Enrofloxacin

MM0395.07 Enrofloxacin N-Oxide Hydrochloride n/a 100mg H C lN

O

O H

O

F

N

N+

O

Escitalopram Oxalate

MM0242.10Imp. H (EP): 3-[(1RS)-5-Cyano-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-1-yl]-N,N-dimethylpropan-1-amine N-Oxide (Citalopram N-Oxide)

63284-72-0 100mg

F

N+

OO

N

MM1162.05Imp. H (EP) as S-Enantiomer: 3-[(1S)-5-Cyano-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-1-yl]-N,N-dimethylpropan-1-amine N-Oxide(Escitalopram N-Oxide)

917482-45-2 100mgN

O

N+

O

F

Esomeprazole Magnesium Trihydrate

MM0095.07Imp. E (EP): 4-Methoxy-2-[[(RS)-(5-methoxy-1H-benzimidazol-2-yl)sulphinyl]methyl]-3,5-dimethylpyridine 1-Oxide (Omeprazole N-Oxide)

176219-04-8 100mgN+

O

O

S

O

NH

N

O















Esomeprazole Sodium

MM0095.07Imp. E (EP): 4-Methoxy-2-[[(RS)-5-methoxy-1H-benzimidazole-2-sulfinyl]methyl]-3,5-dimethylpyridine 1-Oxide (Omeprazole N-Oxide)

176219-04-8 100mgN+

O

O

S

O

NH

N

O

Fentanyl

MM0528.09Imp. A (EP) as Hydrochloride: N-Phenyl-N-[cis,trans-1-oxido-1-(2-phenylethyl)piperidin-4-yl]propanamide Hydrochloride (FentanylN-Oxide Hydrochloride)

n/a 100mg H C l

N+

O

N

O

Fentanyl Citrate

MM0528.09Imp A (EP) as Hydrochloride: (1rs,4rs)-1-(2-Phenylethyl)-4-(N-phenylpropanamido)piperidineN-oxide Hydrochloride (Fentanyl N-OxideHydrochloride)

n/a 100mg H C l

N+

O

N

O

Fexofenadine Hydrochloride

MM0507.19-0025 Fexofenadine N-Oxide Hydrochloride n/a 25mg HClOHN

+

O

OH

O

OH

Flavoxate Hydrochloride

MM0156.07 Flavoxate N-Oxide Hydrochloride n/a 100mg HCl

O ON

+

O

O

O

Flunarizine Dihydrochloride

MM0175.06 Flunarizine N-Oxide Dihydrochloride n/a 100mg 2HCl

N

F

F

N+O

Flupentixol Dihydrochloride

MM0223.08-0025 Flupentixol N1-Oxide n/a 25mgF

N

N + O HO

S

F F

Fluphenazine Dihydrochloride

MM0114.04 Fluphenazine N,N',S-Trioxide Dihydrochloride n/a 100mg2

HClS

N N+

N+

OHO

O

F

F F

O

MM0114.15 Fluphenazine N1-Oxide Dihydrochloride n/a 100mg 2HCl

FF

F

N N

N+

OOH

S

MM0114.18 Fluphenazine Sulfone N1,N4-Dioxide(Fluphenazine N1,N4,S,S-Tetraoxide) 86137-45-3 100mg O

SO

FF

F

N N+

O

N+

OO H

Furaltadone

MM1753.02 Furaltadone N-Oxide Hydrochloride n/a 100mg HCl

ON

+O

ON

N

ON+

O

O

O
















Gefitinib

MM3563.01 Gefitinib N-Oxide 847949-51-3 100mg N+

O

ON

N

NH

F

Cl

O

O

Granisetron Hydrochloride

MM0398.11 Granisetron N-Oxide 160177-68-4 50mgH

H

NH

N N

O

N+

O

Halofantrine Hydrochloride

MM0433.05 Halofantrine N-Oxide 1348409-88-0 100mg F

F F

C l

C l

N+

OOH

Homatropine Hydrobromide

MM1649.02 Homatropine N-Oxide Hydrochloride n/a 100mg N+O

H

H

H

O

O

O H

HCl

AND Enantiomer

Hydrocodone Hydrogen Tartrate 2.5-Hydrate

MM1113.17 Hydrocodone N-Oxide 909265-05-0 100mgO

N+O

H

OO

Hydromorphone Hydrochloride

MM0371.09Imp. B (EP) as Hydrochloride: 4,5 -Epoxy-3-hydroxy-17-methylmorphinan-6-one 17-OxideHydrochloride (Hydromorphone N-OxideHydrochloride)

n/a 100mg HCl

OH

N+O

O O

H

Hydroxychloroquine Sulphate

MM0764.05

Imp. A (EP) as Dihydrochloride: 4-[(7-Chloroquinolin-4-yl)amino]-N-ethyl-N-(hydroxyethyl)pentan-1-amine N-OxideDihydrochloride (Hydroxychloroquine N-OxideDihydrochloride)

n/a 10mg 2HCl

N

NHN

+ OH

O

Cl

Hyoscine Hydrobromide (Scopolamine Hydrobromide)

MM0546.07 Hyoscine N-Oxide Hydrobromide 6106-81-6 100mg HB rO

N+

O

H

HH

O

H

HO

O H

Hyoscyamine Sulfate

MM0794.09 Hyoscyamine N-Oxide Hydrochloride 200721-88-6 100mg HClO

N+

H

O

H

HO

OH














Imipramine Hydrochloride

MM0077.12 Imipramine N-Oxide 6829-98-7 100mg N+

ON

Imiquimod

MM1158.01-0025 Imiquimod N-Oxide 1807607-22-2 25mg

O

N+

N H 2

NN

Ketoconazole

MM0145.07 Ketoconazole N-Oxide 254912-65-7 100mgO N

N+

O O

ClC l

N

N

O

O

AND Enantiomer

Ketotifen Hydrogen Fumarate

MM0180.07Imp. D (EP): 4-[(aRaS)-1-Methylpiperidin-4-ylidene]-4,9-dihydro-10H-benzo[4,5]cyclo-hepta[1,2-b]thiophen-10-one N-Oxide(Ketotifen N-Oxide)

88456-70-6 100mgS

O

N+

O

Lansoprazole

MM0474.07Imp. A (EP): 2-[(RS)-[[3-Methyl-1-oxido-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl]-sulphinyl]-1H-benzimidazole (LansoprazoleN-Oxide)

213476-12-1 100mgN

+

OF

F F

O

S

N H

N

O

MM0474.08 Lansoprazole Sulphone N-Oxide 953787-54-7 100mgN

+

OF

F F

O

S

N H

N

O O

Levodropropizine

MM1246.05 Levodropropizine N-Oxide 152237-40-6 100mg N

N+ OH

OH

O

Levomepromazine Maleate

MM0019.11 Levomepromazine Sulfone N-Oxide(Levomepromazine N,S,S-Trioxide) n/a 50mg N

SO

O

N+

O

O

Lidocaine Hydrochloride Monohydrate

MM0102.01Imp. B (EP): 2-(Diethylazinoyl)-N-(2,6-dimethylphenyl)acetamide (Lidocaine N2-Oxide)

2903-45-9 100mgO

NH

N+

O














Linezolid

MM3300.04 Linezolid N-Oxide 189038-36-6 100mgO

O

NH

O

NF

N+

O

O

Loperamide Hydrochloride

MM0025.09 Imp. F (EP): Loperamide Oxide 106900-12-3 100mgN

+

O

N

O H

C l

O

MM0025.13Imp. G (EP): 4-[cis-4-(4-Chlorophenyl)-4-hydroxy-1-oxidopiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide (Loperamide cis-N-Oxide)

109572-89-6 50mgN

+

O

N

O H

C l

O

Loratadine

MM0257.21 Loratadine N-Oxide 165739-62-8 100mgN

O

O

N+O

Cl

MM0257.22 Loratadine Epoxide N-Oxide 1432057-93-6 100mgN

O

OO

N+O

Cl

Loxapine Succinate

MM1530.04 Loxapine N-Oxide 25967-34-4 100mg N

N+ O

N

O

Cl

Mebhydrolin Napadisilate

MM1891.01 Mebhydrolin N-Oxide 210408-26-7 100mgN

N+

O

Mebrofenin

MM3594.01 Mebrofenin N-Oxide n/a 50mgBr

NH

N+

OHO

O

OH

O

O

Meclozine Dihydrochloride (Meclizine Hydrochloride)

MM0586.05 Meclozine N-Oxide 114624-69-0 10mgCl

N

N+

O














Melperone

MM0321.01 Melperone N-Oxide n/a 100mgO

N+

O

F

Mepacrine Hydrochloride

MM1695.02 Mepacrine N-Oxide Dihydrochloride n/a 100mg 2HCl

NH

N+

O

O

N

Cl

Mepivacaine Hydrochloride

MM0368.06 Mepivacaine N-Oxide n/a 100mg NH

N+

OO

Mepyramine Maleate (Pyrilamine Maleate)

MM0559.06-0025 Mepyramine N-Oxide Maleate n/a 25mgO

OH

O

OHO

N

N

N+ O

Mequitazine

MM3131.01 Mequitazine N-Oxide n/a 100mgN

S

N+ O

H

AND Enantiomer

MM3131.04 Mequitazine Sulfoxide N-Oxide (Mequitazine N,S-Dioxide) 62705-13-9 100mg N

S

O

N+ O

H

AND Enantiomer

MM3131.05 Mequitazine Sulfone N-Oxide (Mequitazine N,S,S-Trioxide) n/a 100mg N

SO O

N+ O

H

AND Enantiomer

Mesoridazine Besilate

MM3617.02 Mesoridazine 5-Sulfoxide N-Oxide (MesoridazineN,S5-Dioxide) n/a 100mg

N+

O

N

S

S

O

O

Methapyrilene Hydrochloride

MM1680.01 Methapyrilene N-Oxide 78761-79-2 100mgN

+N

S

N

O














Methenamine

MM1998.01 Methenamine N-Oxide 62190-92-5 100mgN

N+

NN

O

Metoclopramide Hydrochloride Monohydrate

MM0073.07Imp. G (EP): N'-(4-Amino-5-chloro-2-methoxybenzoyl)-N,N-diethylethane-1,2-diamine N-Oxide(Metoclopramide N-Oxide)

171367-22-9 100mg NH

N+

O

O

ONH 2

Cl

Mianserin Hydrochloride

MM0147.06 Mianserin N-Oxide 62510-46-7 100mgN

+

N

O

Mifepristone

MM1007.02 Mifepristone N-Oxide 91934-98-4 100mgN

+O

OH

H

H

O

Mirtazapine

MM1005.02Imp. A (EP): (14bRS)-2-Methyl-1,2,3,4,10-14b-hexahydropyrazino[2,1-a]pyrido[2,3-c][2]benzazepine 2-Oxide

155172-12-6 100mg N

N

N+

O

Moclobemide

MM0250.03 Moclobemide N-Oxide 64544-24-7 100mgO

C l

NH

N+

O

O

Morphine Hydrochloride

MM0037.03Imp. F (EP): (17S)-7,8-Didehydro-4,5 -epoxy-17-methylmorphinan-3,6 -diol17-Oxide (Morphine N-Oxide)

639-46-3 CS 100mgN

+O

OOH O H

H

Morphine Sulphate

MM0037.03Imp. F (EP): (17S)-7,8-Didehydro-4,5 -epoxy-17-methylmorphinan-3,6 -diol 17-Oxide(Morphine N-Oxide)

639-46-3 CS 100mgN

+O

OOH O H

H













Mycophenolate Mofetil

MM1001.07Imp. G (EP): 2-(Morpholin-4-yl)ethyl (4E)-6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4-enoate N-Oxide

224052-51-1 100mgOH

ON

+

O

O

OO

O

O

Nalbuphine Hydrochloride

MM0341.02 Nalbuphine N-Oxide Hydrochloride n/a 100mg HClOH

O HOOH

N+O

Naloxone Hydrochloride Dihydrate

MM0272.03 Naloxone N-Oxide 112242-14-5 100mgN +O

OOH O

OH

Nefazodone Hydrochloride

MM0591.02 Nefazodone N-Oxide n/a 100mg NN

NN+

N Cl

O

OO

Nevirapine

MM1146.06 Nevirapine N10-Oxide 1027324-99-7 50mgO

N+

N N

NH

O

MM1146.07 Nevirapine N1-Oxide 162255-73-4 100mgNH

N N+

O

N

O

Nicardipine Hydrochloride

MM0465.04 Nicardipine N-Oxide n/a 100mgNH

O

O

ON

+

OO

N+

O

O

Nicotinamide (Niacinamide)

MM0552.02-0025 Imp. E (EP): Pyridine-3-carboxamide 1-Oxide(Nicotinamide N-Oxide) 1986-81-8 25mg N

+NH2

O

O

Nicotine

MM0517.07 Imp. E (EP): (1RS,2S)-1-Methyl-2-(pyridin-3-yl)pyrrolidine 1-Oxide (Nicotine N -Oxide)

491-26-9 100mg N N+

O














MM0517.08 3-[(1S,2S)-1-Methyl-1-oxidopyrrolidin-2-yl]pyridine(Nicotine cis-N'-Oxide) 51095-86-4 50mg

ON

+N

MM0517.19 (1RS,2S)-Nicotine N,N'-Dioxide (3-[(1RS,2S)-1-Methyl-1-oxidopyrrolidin-2-yl]pyridine 1-Oxide) 2055-29-0 100mg N

+N

+

O

O &1

Mixed

Nikethamide

MM0627.02 Nikethamide N-Oxide Hydrochloride n/a 100mg H C lN+

N

O

O

Nizatidine

MM0220.16 Nizatidine Sulfone N-Oxide (Nizatidine N,S,S-Trioxide) n/a 50mg

NH

NH

SS

N+O

N O ON+

O

O

Ofloxacin

MM0228.10

Imp. F (EP) as Hydrochloride: 4-[(RS)-6-Carboxy-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de]-1,4-benzoxazine-10-yl]-1-methylpiperazine 1-Oxide Hydrochloride (Ofloxacin N-OxideHydrochloride)

n/a 100mg H C l

O

N

O

O H

O

F

N

N +

O

Olanzapine

MM0329.03-0025Imp. D (EP): 1-Methyl-4-(2-methyl-10H-thieno-[2,3-b][1,5]benzodiazepin-4-yl)piperazin-1-oxide(Olanzapine N-Oxide)

174794-02-6 25mgN

N+O

N

NH

S

Olopatadine Hydrochloride

MM1261.01-0025(Z)-3-[2-(Carboxymethyl)dibenzo[b,e]oxepin-11(6H)-ylidene]-N,N-dimethylpropan-1-amine Oxide(Olopatadine N-Oxide)

173174-07-7 25mg

O

N+

O

OH

O

MM1261.09(Z)-3-[2-(Carboxymethyl)dibenzo[b,e]oxepin-11(6H)-ylidene]-N,N-dimethylpropan-1-amine OxideHydrochloride (Olopatadine N-OxideHydrochloride)

n/a 100mg H C lO

OH

N+

O

O

Omeprazole

MM0095.07Imp. E (EP): 4-Methoxy-2-[[(RS)-(5-methoxy-1H-benzimidazol-2-yl)sulphinyl]methyl]-3,5-dimethylpyridine 1-Oxide (Omeprazole N-Oxide)

176219-04-8 100mgN+

O

O

S

O

NH

N

O

MM0095.16Imp. I (EP): 4-Methoxy-2-[[(5-methoxy-1H-benzimidazol-2-yl)sulphonyl]methyl]-3,5-dimethylpyridine 1-Oxide(Omeprazole Sulphone N-Oxide)

158812-85-2 100mgN

+

O

O

S

NH

N

O

O O















Opipramol Dihydrochloride

MM0422.03 Opipramol N-Oxide n/a 100mg N N

N+

OHO

MM0422.08 Opipramol Di-N-Oxide n/a 50mg N N+

N+

OHO

O

Oxatomide

MM1115.01 Oxatomide N-Oxide n/a 100mg N

N+ N NH

OO

Oxeladin Hydrogen Citrate

MM0547.01 Oxeladin N-Oxide n/a 10mg OO

N +

O

O

Oxomemazine

MM0958.04 Oxomemazine N-Oxide Hydrochloride(Trimeprazine Sulphone N-Oxide Hydrochloride) n/a 100mg HCl

N N+

OSO

O

Oxybuprocaine Hydrochloride (Benoxinate Hydrochloride)

MM0543.05 Oxybuprocaine N-Oxide Dihydrochloride n/a 100mg 2HCl

ON+

O

O

O

NH2

Oxycodone Hydrochloride

MM0672.06 Oxycodone N-Oxide 71539-52-1 50mgN

+O

OO O

OH

Pantoprazole Sodium Sesquihydrate

MM0099.06 Pantoprazole N-Oxide 953787-60-5 100mgN

+

O

O

O

S

N H

N

O

F

F

O

MM0099.07 Pantoprazole Sulphone N-Oxide 953787-55-8 100mgN

+

O

O

O

S

N H

N

O

F

F

O O

Pefloxacin Mesilate Dihydrate

MM3495.01Imp. D (EP): 4-(3-Carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)-1-methylpiperazine 1-Oxide (Pefloxacin N-Oxide)

85145-21-7 100mgOH

O

N

O

F

N

N+

O

Perphenazine

MM0826.03 Perphenazine N1-Oxide 803615-00-1 100mg S

N N

N+

O HO

C l
















MM0826.05 Perphenazine Sulfoxide N1-Oxide (PerphenazineN1,S-Dioxide) n/a 100mg S

N N

N+

O HO

C l

O

MM0826.09 Perphenazine N1,N4-Dioxide Monohydrochloride n/a 100mg HClS

N N+

N+

OHO

O

Cl

MM0826.08 Perphenazine Sulfoxide N1,N4-Dioxide(Perphenazine N1,N4,S-Trioxide) n/a 100mg O

S

C l

N N+

O

N+

OO H

MM0826.10Perphenazine Sulfoxide N1,N4-DioxideDihydrochloride (Perphenazine N1,N4,S-TrioxideDihydrochloride)

n/a 100mg 2HCl

Cl

N N+

N+

OOH

O

SO

MM0826.11Perphenazine Sulfone N1,N4-DioxideDihydrochloride (Perphenazine N1,N4,S,S-Tetraoxide Dihydrochloride)

n/a 100mg 2HCl

OSO

Cl

N N+

O

N+

OOH

Pheniramine Maleate

MM0059.04 Pheniramine N-Oxide 12656-98-3 100mgN

N+ O

Phenoxybenzamine Hydrochloride

MM0778.04 N-(1-Methyl-2-phenoxyethyl)-1-phenylmethanimine Oxide n/a 100mg O

N+

O

Pioglitazone Hydrochloride

MM0616.09 Pioglitazone N-Oxide 145350-09-0 100mg N+

O

N HS

O

O

O

Pramoxine Hydrochloride

MM3228.01 Pramoxine N-Oxide n/a 100mg N+

O

O

O

O

Pridinol Hydrochloride

MM3493.02 Pridinol N-Oxide n/a 100mgN

+

OO H

Pridinol Mesilate

MM3493.02 Pridinol N-Oxide n/a 100mgN

+

OO H

Procainamide Hydrochloride

MM0550.02 Procainamide N-Oxide Dihydrochloride n/a 100mg2

HClNH

N+ O

O

NH2

















Procaine Hydrochloride

MM0596.02 Procaine N-Oxide 1027072-50-9 100mg ON

+ O

NH 2

O

Prochlorperazine Maleate

MM0411.13Prochlorperazine Sulfone N1,N4-DioxideDihydrochloride (Prochlorperazine N1,N4,S,S-Tetraoxide Dihydrochloride)

n/a 50mg 2HCl

Cl

N N+

O

N+

O

SO

O

Procyclidine Hydrochloride

MM1573.01 Procyclidine N-Oxide n/a 100mgN

+OOH

Promazine Hydrochloride

MM0290.08 Promazine Sulfone N-Oxide (Promazine N,S,S-Trioxide) 26928-74-5 100mg S

N N+

O

OO

Promethazine Hydrochloride

MM0412.05 Promethazine Sulphoxide N-OxideHydrochloride 1135334-50-7 100mg H C l

N

SO

N+ O

Protopine

MM2571.01 Protopine N-Oxide 87264-51-5 100mgO

O

N+

O

O

O

O

Proxymetacaine Hydrochloride

MM0404.02 Proxymetacaine N-Oxide Dihydrochloride n/a 50mg 2HClO

N+

O

O

O

NH2

Quetiapine Fumarate

MM1130.10Imp. H (EP): 2-[2-[4-(Dibenzo[b,f][1,4]thiazepin-11-yl)-1-oxidopiperazin-1-yl]ethoxy]ethanol(Quetiapine N-Oxide)

1076199-40-0 50mg N

N + OO H

O

N

S

MM1130.24 Quetiapine Sulfone N-Oxide (Quetiapine N,S,S-Trioxide) n/a 100mg N

N + OO H

O

N

S

OO

Quinine Dihydrochloride

MM0458.01 Quinine N-Oxide 109906-48-1 100mg O

N

HH

N+

O

OH















MM0458.05 Quinine N,N'-Dioxide (Quinine Di-N-Oxide) 101655-92-9 50mg

O

N+

OH

H

N+

O

OH

Quinine Hydrochloride

MM0458.01 Quinine N-Oxide 109906-48-1 100mg O

N

HH

N+

O

OH

Rabeprazole Sodium

MM0618.04Imp. D (EP): 2-[[(RS)-(1H-Benzimidazol-2-yl)sulfinyl]methyl]-4-(3-methoxypropoxy)-3-methylpyridine 1-Oxide (Rabeprazole N-Oxide)

924663-38-7 100mg S

NH

N

O

N +

O

O

O

MM0618.05Imp. I (EP): 2-[[(1H-Benzimidazol-2-yl)sulfonyl]methyl]-4-(3-methoxypropoxy)-3-methylpyridine1-Oxide (Rabeprazole Sulphone N-Oxide)

924663-37-6 100mg S

NH

N

OO

N +

O

O

O

Raloxifene Hydrochloride

MM0738.01Imp. C (EP): [6-Hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl][4-[2-(piperidin-1-yl)ethoxy]phenyl]methanone N-Oxide (Raloxifene N-Oxide)

195454-31-0 50mgO

N+

O

O

S

OH

OH

Ranitidine Hydrochloride

MM0086.05Imp. E (EP): N-[2-[[[5-[(Dimethyloxidoamino)-methyl]furan-2-yl]methyl]sulphanyl]ethyl]-N'-methyl-2-nitroethene-1,1-diamine (RanitidineN-Oxide)

73857-20-2 100mgO

N+

O

SNH

NH

N+

O

O

Reserpine

MM1423.01 Reserpine N-Oxide 474-48-6 100mgO

N+

H

O

O

O

O

O

O

O

O

H

HNH

O

Rifabutin

MM0633.06 Rifabutin N-Oxide 645406-37-7 100mgN

NH

N+O

OH

O

OO

OH

NH

O OH OO

O

O

Rifampicin (Rifampin)

MM0514.05 Imp. B (EP) as Hydrochloride: Rifampicin N-OxideHydrochloride n/a 100mg HCl

ON

+

NN

OHO

O

O

OO

OHO

NHOH OH

O

OH

Risperidone

MM0491.21 Risperidone cis-N-Oxide n/a 100mg N

N

N+

ON

FO

O















MM0491.22 Risperidone trans-N-Oxide n/a 50mg N

N

N+

ON

FO

O

Rizatriptan Benzoate

MM1313.08Imp. H (EP): N,N-Dimethyl-2-[5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethanamine N-Oxide(Rizatriptan N-Oxide)

260435-42-5 100mgNH

N+O

N

N

N

Roflumilast

MM3618.05 Roflumilast N-Oxide 292135-78-5 50mg NH

N+

Cl

OClO

O

F F

O

Ropinirole Hydrochloride

MM0331.10 Ropinirole N-Oxide Hydrochloride n/a 100mg O

N+

NH

O

H C l

Rotigotine

MM1403.10Imp. E (EP) as Hydrochloride: (2S)-5-Hydroxy-N-propyl-N-[2-(thiophen-2-yl)ethyl]-1,2,3,4-tetrahydronaphthalen-2-amine N-OxideHydrochloride (Rotigotine N-Oxide Hydrochloride)

n/a 50mg HClS

N+

O

OH

Sildenafil Citrate

MM0254.04Imp. B (EP): 5-[2-Ethoxy-5-[(4-methyl-4-oxidopiperazin-1-yl)sulfonyl]phenyl]-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (Sildenafil N-Oxide)

1094598-75-0 100mg SN

N+O

OO

O

N

NH

O

N

N

Solifenacin Succinate

MM1342.04-0025Imp. I (EP): (3R)-3-[[(1S)-1-Phenyl-3,4-dihydroisoquinoline-2(1H)-carbonyl]oxy]-1-azabicyclo[2.2.2]octane 1-Oxide (Solifenacin N-Oxide)

180272-28-0 25mgN

O

O N+

O

Strychnine Nitrate

MM0658.02 Strychnine N-Oxide Hydrochloride 139369-62-3 100mg HCl

N

N+

O

OH

H

H

O

Sulforidazine

MM1195.04 Sulforidazine 5-Sulfone N-Oxide (SulforidazineN,S5,S5-Trioxide) 53926-90-2 100mg

N+

ON

S

SO O

OO














Sulpiride

MM0051.06Imp. F (EP): 1-Ethyl-2-[[(2-methoxy-5-sulphamoylbenzoyl)amino]methyl]pyrrolidine1-Oxide (Sulpiride N-Oxide)

n/a 100mg N+

NH

O

S

O

ON H 2

OO

Sumatriptan Succinate

MM0310.04Imp. D (EP) as Maleate: N,N-Dimethyl-2-[5-[(methylsulfamoyl)methyl]-1H-indol-3-yl]-ethanamine N-Oxide Maleate

n/a 100mgO

OH

O

OHSNH

O ONH

N+

O

Tamoxifen Citrate

MM0053.18 Tamoxifen N-Oxide 75504-34-6 100mgO

N+

O

Terbinafine Hydrochloride

MM0696.12 Terbinafine N-Oxide Hydrochloride n/a 100mg HCl

ON

+

Terconazole

MM1286.03 Terconazole N-Oxide n/a 100mg N + N O ON

N

N

Cl Cl

OO

AND Enantiomer

MM1286.04 Terconazole Di-N-oxide Dihydrochloride n/a 100mg ON + N + O

O

C lC l

N

N

N

O

O

2H C l

AND Enantiomer

Terfenadine

MM0055.15 (S)-Terfenadine N-Oxide n/a 25mgOH

N+

O

OH

Tetracaine Hydrochloride

MM0504.02 Tetracaine N-Oxide 55750-02-2 100mg ON + O

O

NH

Thebaine

MM0244.01 Thebaine N-Oxide 81600-02-4 100mgN+O

OO O

Thioridazine Hydrochloride

MM0116.07 Thioridazine N-Oxide 103827-30-1 50mg N+

O

N

S

S















Ticlopidine Hydrochloride

MM0150.16 Ticlopidine N-Oxide 79923-55-0 100mg N+

S

ClO

Tramadol Hydrochloride

MM0007.11 Tramadol N-Oxide 147441-56-3 100mg OHO

N+

O

AND Enantiomer

Trazodone Hydrochloride

MM0421.13

Imp. A (BP) as Hydrochloride: 4-(3-Chloro-phenyl)-1-[3-(3-oxo-2,3-dihydro-1,2,4-triazolo[4,3-a]pyridin-2-yl)propyl]piperazineN1-Oxide Hydrochloride (Trazodone N-OxideHydrochloride)

55290-66-9 50mg HClClN

N+

N

NN

O O

Trifluoperazine Hydrochloride

MM0441.07 Trifluoperazine Sulfoxide N1,N4-Dioxide(Trifluoperazine N1,N4,S-Trioxide) 150111-58-3 100mg

FF

F

N N+

O

N+

O

SO

MM0441.08 Trifluoperazine N4-Oxide Dihydrochloride n/a 100mg 2HCl

FF

F

N N

N+

O

S

MM0441.09 Trifluoperazine Sulfone N1,N4-Dioxide(Trifluoperazine N1,N4,S,S-Tetraoxide) n/a 100mg

FF

F

N N+

O

N+

O

S

O

O

MM0441.11 Trifluoperazine N1,N4-Dioxide 150111-57-2 100mgFF

F

N N+

O

N+

O

S

MM0441.12 Trifluoperazine N1-Oxide 52172-24-4 100mg S

N N+

N

O

F

F F

Triflupromazine Hydrochloride

MM1675.04 Triflupromazine Sulfoxide N-Oxide(Triflupromazine N,S-Dioxide) 94163-91-4 100mg

FF

F

N N+

OSO

MM1675.08 Triflupromazine N-Oxide Hydrochloride n/a 100mg HClS

N N+

O

F

F F

MM1675.09 Triflupromazine Sulfone N-Oxide Hydrochloride(Triflupromazine N,S,S-Trioxide Hydrochloride) n/a 100mg HClSO

O

N N+

O

F

F F
















Trihexyphenidyl Hydrochloride

MM0237.04 Trihexyphenidyl N-Oxide 161564-79-0 50mg N+

OO H

Trimebutine Maleate

MM0417.17 Trimebutine N-Oxide Hydrochloride n/a 100mgO

O

ON +

O

O

O

H C l

Trimeprazine Tartrate (Alimemazine Tartrate)

MM0958.04 Trimeprazine Sulphone N-Oxide Hydrochloride(Oxomemazine N-Oxide Hydrochloride) n/a 100mg HCl

N N+

OSO

O

MM0958.08 Trimeprazine N-Oxide Hydrochloride n/a 100mg HClS

N N+

O

MM0958.07 Trimeprazine Sulfoxide N-Oxide (TrimeprazineN,S-Dioxide) n/a 100mg N N

+

OSO

Trimetazidine Dihydrochloride

MM0539.13 Trimetazidine N-Oxide Dihydrochloride n/a 100mg 2HCl

O

O

O

N+

NH

O

Trimethobenzamide Hydrochloride

MM3281.02 Trimethobenzamide N-Oxide n/a 100mg ON

+ON

H

O

O

O

O

Trimipramine Maleate

MM0240.04Imp. A (EP): (2RS)-3-(10,11-Dihydro-5H-dibenzo-[b,f]azepin-5-yl)-N,N,2-trimethylpropan-1-amineN-oxide (Trimipramine N-Oxide)

14171-70-1 100mg N+

NO

Tripelennamine Hydrochloride

MM1631.01 Tripelennamine N-Oxide 60317-19-3 100mgN

NN

+O

Tropicamide

MM0601.06-0025 Tropicamide N-Oxide Hydrochloride n/a 25mg HCl

N+

O

N

OH

O

Vardenafil Hydrochloride Trihydrate

MM1569.03 Vardenafil N-Oxide 448184-48-3 100mg NN

O

NH

NS

OO

N

N+

OO
















Venlafaxine Hydrochloride

MM0393.14 Venlafaxine N-Oxide 1094598-37-4 100mg N+ O

OH

O

Vincamine

MM0519.02 Vincamine N-Oxide 51442-60-5 100mgN

+

N

OO

OH

H O

Vinpocetine

MM0406.06 Vinpocetine N-Oxide 109741-24-4 100mg NN

+

OH

O

O

Xanthinol Nicotinate

MM1048.01 Xanthinol N-Oxide n/a 100mgN

O

N

N+

OH

O

OH

NNO

Zolmitriptan

MM0298.05Imp. B (EP): N,N-Dimethyl-2-[5-[[(4S)-2-oxo-1,3-oxazolidin-4-yl]methyl]-1H-indol-3-yl]ethan-1-amine N-Oxide (Zolmitriptan N-Oxide)

251451-30-6 100mgNH

N+

O

N HO

O

Zopiclone

MM0149.01Imp. A (EP): (5RS)-6-(5-Chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl 4-Methylpiperazine-1-carboxylate 4-Oxide(Zopiclone Oxide)

43200-96-0 100mg N

Cl

N

ON

N

O

O

N

N+

O










4

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Formation of Omeprazole Sulphone by oxidative degrada-tion of Omeprazole (Imp. D (EP): 5-Methoxy-2-[[(4-meth-oxy-3,5-dimethylpyridin- 2-yl)methyl]sulphonyl]-1H-ben-zimidazole (Omeprazole Sulphone), MM0095.05)

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